4-tert-butyl-5-{3-[cyano(methoxycarbonyl)methyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran

Base Information

Chemical Name:4-tert-butyl-5-{3-[cyano(methoxycarbonyl)methyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran
CAS No.:526197-99-9
Molecular Formula:C₂₀H₂₅NO₃
Molecular Weight:327.423
Hs Code.:

Synonyms:4-tert-butyl-5-{3-[cyano(methoxycarbonyl)methyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran

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Chemical Property of 4-tert-butyl-5-{3-[cyano(methoxycarbonyl)methyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran

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Technology Process of 4-tert-butyl-5-{3-[cyano(methoxycarbonyl)methyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran

There total 5 articles about 4-tert-butyl-5-{3-[cyano(methoxycarbonyl)methyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 866129-75-1
5-[3-(bromomethyl)phenyl]-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran

: 526197-99-9
4-tert-butyl-5-{3-[cyano(methoxycarbonyl)methyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: 76.4 percent / tetra-n-butylammonium hydrogen sulfate / tetrahydrofuran; H₂O / 28 h / Heating

2: 93.7 percent / NaH / toluene / 1 h

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; In tetrahydrofuran; water; toluene; 2: Claisen condensation;
DOI:10.1016/j.tet.2005.07.081

Reference yield:

: 866129-66-0
5-(3-bromophenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran

: 526197-99-9
4-tert-butyl-5-{3-[cyano(methoxycarbonyl)methyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 96.3 percent / tetrahydrofuran; hexane / 0.5 h

2.1: 96 percent / NaBH₄ / CH₂Cl₂; methanol / 0.5 h

3.1: 94.3 percent / CBr₄; PPh₃ / tetrahydrofuran / 0.5 h / 20 °C

4.1: 76.4 percent / tetra-n-butylammonium hydrogen sulfate / tetrahydrofuran; H₂O / 28 h / Heating

5.1: 93.7 percent / NaH / toluene / 1 h

With sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; 5.1: Claisen condensation;
DOI:10.1016/j.tet.2005.07.081

Reference yield:

: 866129-69-3
4-tert-butyl-5-(3-formylphenyl)-3,3-dimethyl-2,3-dihydrofuran

: 526197-99-9
4-tert-butyl-5-{3-[cyano(methoxycarbonyl)methyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / NaBH₄ / CH₂Cl₂; methanol / 0.5 h

2: 94.3 percent / CBr₄; PPh₃ / tetrahydrofuran / 0.5 h / 20 °C

3: 76.4 percent / tetra-n-butylammonium hydrogen sulfate / tetrahydrofuran; H₂O / 28 h / Heating

4: 93.7 percent / NaH / toluene / 1 h

With sodium tetrahydroborate; carbon tetrabromide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 4: Claisen condensation;
DOI:10.1016/j.tet.2005.07.081